Generation of Sulfamoyl Radicals via Visible-Light Mediated Fixation of Sulfur Dioxide for the Synthesis of Sulfonamides

Autor(es)

Arroio, Thais Rodrigues ; Nau, Jan Philipp ; Hofman, Kamil ; Foerster, Christoph ; Faber, Stephanie L. ; Becker, Sabine ; Heinze, Katja ; Clososki, Giuliano Cesar ; Manolikakes, Georg

• Tipo de documento: Artigo Científico
• Fonte: ADVANCED SYNTHESIS & CATALYSIS; v. 367, n. 1, p. 6-pg., 2024-11-20.

Resumo

Herein, we report a new approach for the light-mediated generation of sulfamoyl radicals using sulfur dioxide as key building block and the direct application of these radicals in the synthesis of sulfonamides. In the presence of different photoredox catalysts, sulfamoyl radicals can be generated directly from SO2 or the SO2 surrogate DABSO (1,4-diazabicyclo[2.2.2]octane & sdot;bis (sulfur dioxide) adduct) and N-aminopyridinium salts as nitrogen radical precursors. Trapping of the in situ generated sulfamoyl radicals with selected electron-rich olefins affords different sulfonamides in up to 86% yield in a three-component procedure. This transformation provides a complementary approach for the in situ generation of sulfamoyl radicals as synthetic intermediates for the assembly of the sulfonamide functionality, a privileged motif in active pharmaceutical ingredients. (AU)

• Processo FAPESP: 20/13962-9 - Estudos sintéticos visando a preparação de novos piridoindois de interesse medicinal
• Beneficiário: Thais Rodrigues Arroio
• Modalidade de apoio: Bolsas no Brasil - Doutorado
• Processo FAPESP: 22/08837-6 - Síntese de (Hetero)arilsulfonamidas via sulfamoilação C-H fotocatalisada usando radicais sulfamoilas
• Beneficiário: Thais Rodrigues Arroio
• Modalidade de apoio: Bolsas no Exterior - Estágio de Pesquisa - Doutorado